CHATHAM: CAPE COD’S BEST FAMILY VACATION TOWN
When you hear Cape Cod family vacation, what do you picture? Maybe sandy beaches, ice cream cones and that Americana summer feel? And, you’d be exactly right. Cape Cod is one of those destinations that gives off quintessential East Coast summer vibes. It just feels easy and relaxing, and it’s the perfect trip for families with little ones.
As I was searching for a place that would be great for our kids, ages 2.5 and 10 months, I wanted somewhere that felt effortless for us as parents but still gave us a nostalgic-type of summer. A place that screamed summer with beaches, slow mornings, and East coast charm that we’d remember forever. That place turned out to be Chatham in Cape Cod and I honestly can’t recommend it enough. It was the perfect mix of adventure and relaxation for our two small kids.
Take a look at all things Chatham.
GETTING TO CAPE COD
Flying into Boston is the easiest route, then it’s about a 1.5–2 hour drive to Chatham (depending on traffic). We drove in on a Monday, which made for a smooth ride, but weekends can get a bit congested with summer travelers. You can also fly into Chatham, but with two kids, I didn’t want to deal with a layover and another flight, so we rented a car.
I always rent through rentalcars.com! The drive itself is beautiful and really sets the tone for that classic Cape Cod feel.
WHERE TO STAY IN CHATHAM
Chatham has two standout spots for a perfect family stay: Chatham Bars Inn and Wequassett Resort. We chose Wequassett, and we couldn’t be happier with our choice. It felt more kid-friendly, with activities and spaces that made traveling with small children a breeze.
From the moment we arrived with cribs and little toys for the boys ready in our room, to their welcoming attitude toward our children at all their restaurants, including their Michelin-starred dining, and the abundance of kid-friendly activities, this property exceeded our expectations and is one we will definitely return to.
You can book your stay at Wequassett here or browse other options in the area, use the booking finder below.
WHAT TO DO IN CHATHAM, MA
The beaches are the big draw for a Cape Cod family vacation but a stay at Wequassett in Chatham comes with so much more to explore. Check out some of our favorite activities.
+ SOIREE ON THE BAY
This was one of my favorite experiences in Chatham. Soiree on the Bay happens every Monday at Wequassett and it’s one of those events that you picture when you think of Cape Cod. Perfect for unwinding with a glass of wine while the kids play safely nearby. As the sun sets over the water, the views are simply unforgettable. It was a great start to our trip.
+ POOL TIME
Wequassett’s pool was an absolute hit with our kids. Meyer loved splashing around while we got to relax, and every morning he woke up asking to go to the ‘agua park.’ It’s safe to say he fell in love. The pool is stocked with toys and floaties, so kids have everything they need for endless fun.
And then there’s the ice cream man, who makes daily stops at 2 and 4 p.m. Watching the kids’ excitement as they picked their favorite treat was pure joy. It’s little touches like this that make Wequassett so family-friendly and truly memorable.
+ WEQUASSETT BEACHES
The on-site beach is wonderful, but the off-site, secluded beach is next-level. They have a boat shuttle that takes you there (you’ll have to book this in advance). They even pack a lunch, set up chairs, and provide everything you need to make the day seamless. Our kids loved having the space to run around, and it felt stress-free for us as parents.
+ SUNSET SAIL
A sunset sail is a must-do for families visiting Chatham. The views of the coastline from the water are breathtaking, and it’s a gentle, calm experience perfect for kids who aren’t ready for high-energy adventures.
+ SEAL WATCHING OR SHARK ALLEY TOUR
Both tours are incredible ways to get close to Cape Cod’s wildlife. Kids are mesmerized by seals popping up in the water, and the Shark Alley tour adds a little educational adventure. These trips are interactive, fun, and easy for families with little ones to enjoy. You can book both of these experiences directly with Wequassett.
+ KIDS SPLASH PAD
The on-site splash pad and jungle gym at Wequassett is huge. It’s a pirate ship setup that kept our toddler entertained every day. When you aren’t at the pool or beach, this area is a great place to play.
+ CHATHAM TOWN & LIGHTHOUSE
Chatham itself is charming, with a lighthouse that’s perfect for a short stroll and lots of boutique shops to explore. We stumbled upon a hidden coffee spot that became our daily ritual. The town feels like stepping into a postcard.
+ CHATHAM BEACHES
Chatham and Cape Cod are home to several famous beaches that are great for a family vacation and well worth exploring. Some even offer morning yoga sessions, making for a perfect start to the day. Here are a few public beaches you won’t want to miss: Harding’s Beach, Nauset Beach and Chatham Lighthouse Beach.
+ NANTUCKET DAY TRIP
If you have time, a day trip to Nantucket is a must-do, but plan for a full day. The ferry ride is an adventure in itself, and the island is charming, with cobblestone streets and quaint shops. Kids will enjoy the novelty, and you will love the scenery and island culture.
WHERE TO EAT IN CHATHAM
Dining at Wequassett was such a treat. We were able to try nearly every restaurant on-site and here’s our thoughts on each (spolier alert: we loved them all).
- Twenty Eight Atlantic – Absolutely the best (And Cape Cod’s only Forbes Five-Star restaurant), and they surprisingly were so great with our two small kids.
- Breakfast at Wequassett – In the dining room of 28 Atlantic; kids have their own pirate ship buffet complete with hats and eye patches. The thoughtful touches for little ones are everywhere.
- Verandah’s – Perfect outdoor seating for a relaxed dinner.
- Outer Bar and Grille – Great for casual dining right by the pool
- The Sill – Their newest grab and go stop onsite. We went here for coffee every day!
- Thoreau’s – We didn’t get a chance to eat here, but it’s more of a hidden gem on the property. A dimly lit elegant vibe.
Chatham, Cape Cod ended up being the perfect family vacation with a combination of nostalgic summer vibes, kid-friendly adventures, and easy-going luxury. From beaches to sunset sails to thoughtful touches at our resort, it’s a destination that truly makes summer feel effortless even with little ones in tow.
Got questions? Reach out on Instagram!
happy travels, liz stanford
Disclosure: Some of these links are affiliate links, which means when you purchase something using these links, I may earn a small commission at no additional cost to you. However, I only link these companies because I have used them or truly recommend them based on their quality and the experience I had.
